The End of The Office: Entertainment at Its Most Awkward

As The Office series finale approaches, we prepare to say goodbye to a show known for making comedy out of the most uncomfortable situations. Who among us haven’t covered our shaking heads with our hands as we watched in despair as one of our favorite Dunder Mifflin employees makes an extremely awkward situation even worse? As much as we have wanted to turn away, we have kept watching The Office, entertainment being found in the most painful of circumstances. The one-hour season finale airs May 16 on NBC, but until then, let us relive just a few of the most cringe-worthy moments from the past nine seasons of one of the most influential shows on television.

Diversity Day

One of the first extremely awkward moments can be found in this episode from the very first season, where Michael Scott tries to make a point about racial diversity to his employees — by greatly offending one of them. It served as a glimpse of many seasons of inappropriateness to come.

Niagara

At Jim and Pam’s wedding rehearsal dinner, everyone is sworn to secrecy about Pam’s pregnancy so as not to offend her grandmother. Michael Scott is in attendance, so of course it is expected to not end well. No one is more surprised than Jim, though, when it is he who accidentally reveals the truth. Michael tries to make things better, but of course, only makes it much, much worse. You weren’t expecting a problem-free wedding were you? That would be no fun at all.

Scott’s Tots

Of all of Michael Scott’s blunders, and there have been many, perhaps the most agonizing was this one from season six. Ten years after promising to pay the college tuition of a group of disadvantaged youths upon their graduating high school, he must face them and admit that he cannot fulfill his promise. Having to watch unwarranted praise and thanks showered upon Michael before his final admission makes this episode very difficult to watch.

Suit Warehouse

Just when you think someone has finally overcome their own limitations to finish on a triumphant note, it all goes terribly wrong in one swift, horrible motion. Such was the case after Darryl Philbin’s job interview in Philadelphia. After a somewhat shaky start, he is offered the job. What is supposed to be a victory basketball shot to celebrate his success results in the death of the fish in the office aquarium. Oops. In life, no real victory comes without some struggle, and this has certainly always been the case on The Office.

Has there been one moment that has just made you want to look away? Tell us, what is your favorite unforgettable awkward moment from The Office?